Accepting the worst

There’s an exhilarating freedom and motivation in having nothing to lose. History is full of amazing tales of underdog ingenuity. Likewise, stereotypes abound of the mighty falling flat, trying desperately to protect what they’ve got.

But even more insidious than actively trying to protect what you have, is frequent fretting about how to do so in your mind. It’s so easy to fall into an endless churn of worries about how your precious gains could vanish tomorrow.

This is known as loss aversion. It’s the default routing of our evolutionary brains, and it can lead to unnecessary stress, lost opportunities, and poor decision-making. But it doesn’t have to be your destiny – it is indeed possible to reroute.

The stoic practice of negative visualization is one way to do this. If you imagine, clearly and frequently, the worst case scenario, you can work on coming to terms with its consequences. Usually they’re far less dire than your worries would lead you to believe.

I’ve employed this technique from the get-go with everything I hold dear in my life. As an example, here’s how I’ve applied this to the thought that a terrible end could prematurely doom Basecamp.

It’s easy to contemplate all sorts of spectacular ways this could happen: A massive hack that destroys all data, all backups. Some sort of epic fraud that indicts the entire company. I let my mind seek out all sorts of terrible corners.

Then I consider what’s left: I got to work with amazing people for over a decade. I grew as a programmer, as a manager, and as a business person immensely. I enjoyed most days, most of the time. I helped millions of people be more productive doing all sorts of wonderful things.

I’m so much better off for having been through this, regardless of how a possible end might occur for the company. This makes whether circumstances allow us to continue for another decade (or five!) a lesser deal than the fact that we did for one.

This brings a calmness, a tranquility as the stoics would say, that’s incredibly liberating. A head free of fear or dread. I believe this not only is a saner, healthier way to live (stress wrecks havoc on the body and soul), but also better for the company.

We’re not running Intel, and I don’t want to have Grove’s “only the paranoid survive” as my modus operandi. I want to retain the underdog sense of having nothing to lose, even when conventional thought might say I (and the company) have everything to lose.

Aditya Rustgi

on 01 Dec 14

I’ve been thinking about exactly the same topic over the thanksgiving weekend. When you recognize what you are thankful for, you also realize that you have so much you could lose.

The biggest sense of fear comes from the feeling that if you deviate from a path that you have to an end that you hold dear, that you may never get around to getting back on the path. It leads to a fixation on the path, and worse still a fixation on the end.

That fixation is what I am trying to remove myself from.

You article provides some hints. Focus on the unchangeable, both about the path and end. The skills, the relationships, the learnings.

Félix Jofré

on 01 Dec 14

This post comes to me with great timing. A big meeting is coming and I’ve been feeling terrified and stressed over the thought of losing everything we’ve built in our startup, but most importantly, to disappoint my employees and co-founders.

As a CEO, I feel like my first job is to protect these people and this task can become very overwhelming, specially for the fact that in times of crisis you don’t really get to tell and share your feelings, you don’t get to tell you’re afraid or worried because that would usually make things worse. It feels like shit to deal with this constant risk, and it’s already hard enough to be honest to yourself and figure out all these issues could’ve been avoided with better managing. At the end, it feels that all the issues and faults are mine and product of my decisions, even if there might be someone else’s big fuck ups.

Yet is in this exact moment of storm shit where I have to be smart and cold enough to step aside from my emotions in order to make the best decision and take the best actions that will give us a chance at recovering. I’ve been trying to figure out and even help the visualization with drawings (ha) of the worst case scenario. At the beginning it really hurts your stomach, physically… but after time and thought, I too believe it really helps. Perspective prepare and strengths you.

Having things to lose is a huge burden and it really make me miss the times when I was all on my own, doing small things by myself and knowing the only one that had to pay the price of an end would be me. Yet I know I have to learn how to build a mindset to recover the agility and peace of mind. Otherwise this would be no way of living. Health comes first.

Thanks for the insight David, have a good day.

twiz

on 01 Dec 14

It’s a breath of fresh air to see this among other company blogs e.g. “6 simple ways to boost conversion..”

Anonymous Coward

Dennis Payonk

on 03 Dec 14

I think this is the best type of analysis to do for quantitatively oriented individuals. I’ve been using this practice since college exams.

Also, I find this works well in the time leading up to what I’d call fixed moments. If you’re worried about a big meeting or an important presentation, just consider that no matter what you do, it will be over in less than a day (or whatever time period it may be).

I do this often enough & see other people do the same. Interestingly, these people all tend to be optimists. There is something soothing about following the rabbit hole versus worrying about an ambiguously bad circumstance.

This discussion is closed.

About David

Creator of Ruby on Rails, partner at 37signals, best-selling author, public speaker, race-car driver, hobbyist photographer, and family man.